The park surrounds two inactive reservoirs, Spot Pond and the Fells Reservoir, and the three (North, Middle, and South) active reservoirs supplying the town of Winchester. Spot Pond and the Fells Reservoir are part of the Wachusett water system, one of six primary water systems that feed metropolitan Boston's waterworks.

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The area around Middlesex Fells is known to have been explored by John Winthrop, Governor of the Massachusetts Bay Colony, in 1632.[3] The reservation's lands have been used for the production of timber, granite, and ice. Abundant water power meant that many mills, including one that manufactured some of the first vulcanized rubber products, were located here. Remnants of early mill works are visible in the Spot Pond Archeological District, located in the Virginia Woods section, the site of the former mill village of Haywardville.

The reservation was initiated in 1891 with the donation of Virginia Wood to The Trustees of Reservations "by Mrs. Fannie Tudor as a memorial to her daughter, Virginia, who had died in a horse riding accident in the forest. The property was later donated to the Metropolitan District Commission in 1923."[4] In 1893, the state took the property over and began managing it as a state park.

The reservation has over 100 miles of trails for hiking, mountain biking, cross-country skiing, and horseback riding. Trailheads are accessible from Interstate 93 at exits 33 and 34, and 35 Southbound. Fishing is offered on Dark Hollow Pond. Other facilities include picnicking areas, an observation tower, and a tot lot. A concessionaire offers sailing lessons and rentals of kayaks, canoes, pedal boats and row boats on Spot Pond during summer.[6] Rock climbing is also popular in the Fells.[3]